#4 1993: Apple Newton

The Newton platform was a personal digital assistant (PDA) developed by Apple in 1987. It’s the predecessor for modern day Smartphones.

The project missed its original goals to reinvent personal computing, and then to rewrite contemporary application programming. The Newton project fell victim to project slippage, scope creep, and a growing fear that it would interfere with Macintosh sales. According to former Apple CEO John Sculley, the corporation invested approximately US$100M to develop Newton, but when Steve Job returned to Apple as its CEO, first thing he did was to scrape the project that already gulped in lots of money with profit.

#3 1999: LiveJournal

LiveJournal combined blogging and social networking. It was started on April 15, 1999 by American programmer Brad Fitzpatrick as a way of keeping his high school friends updated on his activities.

It was supposed to have the popularity and money as that of Facebook or Google by now. But LiveJournal never became a giant of the Web 2.0 era, perhaps due to a combination of management missteps and a user base that was not much in to internet. The site's Wikipedia page mentions some of the goof-ups, among them the controversial addition of advertising on non-free accounts, a year after management promised not to put advertising on the site.

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